ethyl 5-(4-(trifluoromethyl)phenyl)-4,5-dihydroisoxazole-3-carboxylate | 737790-81-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl 5-(4-(trifluoromethyl)phenyl)-4,5-dihydroisoxazole-3-carboxylate
• 英文别名: ethyl 5-[4-(trifluoromethyl)phenyl]-4,5-dihydro-1,2-oxazole-3-carboxylate
• CAS: 737790-81-7
• 化学式: C₁₃H₁₂F₃NO₃
• 分子量: 287.238
• InChiKey: WWWSJJPBJGEKKY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  47.9
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ethyl 5-(4-(trifluoromethyl)phenyl)-4,5-dihydroisoxazole-3-carboxylate 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 8.0h， 生成 (5-(4-(trifluoromethyl)phenyl)-4,5-dihydroisoxazol-3-yl)methanol
  参考文献：
  名称：

  [EN] SUBSTITUTED HETEROCYCLIC COMPOUNDS USEFUL IN THE TREATMENT OF CARDIOVASCULAR DISEASES
  [FR] COMPOSES HETEROCYCLIQUES SUBSTITUES UTILES POUR LE TRAITEMENT DE MALADIES CARDIO-VASCULAIRES

  摘要：

  其中：a.o. T是氧、硫或NR11，其中R11是氢或较低的烷基；V是-N<，-CH<或-NH-CH<；X1是氢，可选择取代的较低烷基，可选择取代的环烷基，可选择取代的芳基或可选择取代的杂芳基；X2是可选择取代的芳基或可选择取代的杂芳基；Y是可选择取代的二氢杂芳基；Z1和Z2分别是1-4个碳原子的可选择取代的烷基，用于治疗各种疾病状态，特别是心血管疾病，如心房和心室心律失常、间歇性跛行、普林兹梅塔（变异）心绞痛、稳定和不稳定心绞痛、运动诱发性心绞痛、充血性心脏病和心肌梗死。这些化合物还可用于治疗糖尿病。

  公开号：

  WO2004069818A1
• 作为产物：
  描述：

  重氮乙酸乙酯 、 对三氟甲基苯乙烯 在 亚硝酸特丁酯 、 六氟异丙醇 、 tetrabutylammonium tetrafluoroborate 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以66%的产率得到ethyl 5-(4-(trifluoromethyl)phenyl)-4,5-dihydroisoxazole-3-carboxylate
  参考文献：
  名称：

  Synthesis of Isoxazolines and Oxazines by Electrochemical Intermolecular [2 + 1 + n] Annulation: Diazo Compounds Act as Radical Acceptors

  摘要：

  Reported herein is an unprecedented synthesis of isoxazolines and oxazines through electrochemical intermolecular annulation of alkenes with tert-butyl nitrite, in which diazo compounds serve as radical acceptors. Notably, [2 + 1 + 2] and [2 + 1 + 3] annulations occur when styrenes and allylbenzenes are used as substrates, respectively. The latter reaction undergoes group migration to form more stable radical, manifesting radical route instead of conventional 1,3-dipolar cycloaddition occurs. Moreover, scale-up experiments suggest the potential application value of these transformations in industry.

  DOI：

  10.1021/acs.orglett.9b03306

文献信息

• Oxidize Amines to Nitrile Oxides: One Type of Amine Oxidation and Its Application to Directly Construct Isoxazoles and Isoxazolines
  作者：Xiao-Wei Zhang、Xiao-Lin He、Nan Yan、Hong-Xing Zheng、Xiang-Guo Hu

  DOI：10.1021/acs.joc.0c02281

  日期：2020.12.4

  A facile oxidative heterocyclization of commercially available amines and tert-butyl nitrite with alkynes or alkenes leading to isoxazoles or isoxazolines is described. The unprecedented strategy of the oxidation of an amine directly to a nitrile oxide was used in this cyclization process. This reaction is highly efficient, regiospecific, operationally simple, mild, and tolerant of a variety of functional

  描述了可商购的胺和亚硝酸叔丁酯与炔或烯烃的容易的氧化性杂环化，其导致异恶唑或异恶唑啉。在这种环化过程中使用了前所未有的将胺直接氧化为一氧化氮的策略。该反应是高效的，区域特异性的，操作简单的，温和的，并且耐受多种官能团。对照实验为这种新型的氧化环化反应提供了一种一氧化氮中间体机制。此外，实现了对生物活性分子骨架的合成应用和药物的后期修饰。
• Substituted heterocyclic compounds
  申请人：——

  公开号：US20030176447A1

  公开（公告）日：2003-09-18

  Disclosed are novel heterocyclic derivatives, useful for the treatment of various disease states, in particular cardiovascular diseases such as atrial and ventricular arrhythmias, intermittent claudication, Prinzmetal's (variant) angina, stable and unstable angina, exercise induced angina, congestive heart disease, and myocardial infarction. The compounds are also useful in the treatment of diabetes, and for increasing HDL plasma levels in mammals.

  揭示了一种新颖的杂环衍生物，用于治疗各种疾病状态，特别是心血管疾病，如心房和心室心律失常、间歇性跛行、普林兹梅塔（变异）心绞痛、稳定和不稳定心绞痛、运动诱发性心绞痛、充血性心力衰竭和心肌梗死。这些化合物还可用于治疗糖尿病，并可增加哺乳动物的高密度脂蛋白血浆水平。
• [EN] SUBSTITUTED PIPERAZINE COMPOUNDS AND THEIR USE AS FATTY ACID OXIDATION INHIBITORS<br/>[FR] COMPOSES DE PIPERAZINE SUBSTITUES ET LEUR UTILISATION EN TANT QU'INHIBITEURS DE L'OXYDATION D'ACIDES GRAS
  申请人：CV THERAPEUTICS INC

  公开号：WO2003008411A1

  公开（公告）日：2003-01-30

  Disclosed are novel heterocyclic derivatives of the formula (I), wherein amongst others R?1, R2, R3, R4, R5, R6, R7, and R8¿ are hydrogen; T is oxygen, sulfur, or NR11, in which R11 is hydrogen or lower alkyl; V is N<, -CH<, or N-CH<; X1 is hydrogen, optionally substituted lower alkyl, optionally substituted cycloalkyl, optionally substituted aryl, or optionally substituted heteroaryl; X2 is optionally substituted aryl or optionally substituted heteroaryl; Y is optionally substituted monocyclic heteroarylenyl; and Z?1 and Z2¿ are independently optionally substituted alkylene or 1-4 carbon atoms. The compounds are useful for the treatment of various disease states, in particular cardiovascular diseases such as atrial and ventricular arrhythmias, intermittent claudication, Prinzmetal's (variant) angina, stable and unstable angina, exercise induced angina, congestive heart disease, and myocardial infarction. The compounds are also useful in the treatment of diabetes, and for increasing HDL plasma levels in mammals.

  本发明涉及一种新型杂环衍生物的公开式（I），其中，R1、R2、R3、R4、R5、R6、R7和R8中的一些是氢；T为氧、硫或NR11，其中R11为氢或低碳基；V为N<、-CH<或N-CH<；X1为氢、可选取代的低碳基、可选取代的环烷基、可选取代的芳基或可选取代的杂环芳基；X2为可选取代的芳基或可选取代的杂环芳基；Y为可选取代的单环杂芳基；Z1和Z2独立地为可选取代的烷基或1-4碳原子。该化合物可用于治疗各种疾病状态，特别是心血管疾病，如心房和心室心律失常、间歇性跛行、普林兹梅塔尔（变异型）心绞痛、稳定和不稳定性心绞痛、运动诱发性心绞痛、充血性心力衰竭和心肌梗死。该化合物还可用于治疗糖尿病，并可提高哺乳动物的高密度脂蛋白血浆水平。
• SUBSTITUTED PIPERAZINE COMPOUNDS AND THEIR USE AS FATTY ACID OXIDATION INHIBITORS
  申请人：CV THERAPEUTICS, INC.

  公开号：EP1406898A1

  公开（公告）日：2004-04-14
• SUBSTITUTED HETEROCYCLIC COMPOUNDS
  申请人：CV Therapeutics Inc.

  公开号：EP1583760A2

  公开（公告）日：2005-10-12